Organic I Exam 2 - City University of New Yorkuserhome.brooklyn.cuny.edu/rpmurelli/s2018 Organic I...
Transcript of Organic I Exam 2 - City University of New Yorkuserhome.brooklyn.cuny.edu/rpmurelli/s2018 Organic I...
S2018OrganicChemistryIMid-TermExam2Name(print):Name(Sign):RecitationInstructorName(sowecangetitbacktoyou):Instructions1.Keeptheexamcloseduntilyouareinstructedtobegin.2.Theexamconsistsof5questions.Thefirstthingyoushoulddoismakesurethatnopagesaremissing.Ifapageismissing,notifyaproctorimmediately.3.Youwillhave1hrand15minutestocompletetheexam,atwhichtimepencilsmustbeputdown.Budgetyourtimewisely.4.Makesuretoshowallofyourwork,andmakeitclearwhatyourthoughtprocesswas.Answersshouldfitinthespaceprovided.Ifyouneedtousethebackofthesheetofpaper,youmustmakenoteofitinthespaceallottedforcredit.
Breakdown
1.____/20
2.____/203.____/104._____/305._____/20
total_____/100
1)ReactionsPartA.Showtheproductsofthefollowingreactions.Chose5ofthe6,andmakesuretocirclethoseyouwantgraded.Ifyoudonotcircle,wewillgradethefirst5.(20points,4each)
Me Br2
H2O
CH2Br2
Zn
Br Mg(0)
Me MeNa/NH3
BH3; NaOOH
Br
NaNH2
E2
(A)
(B)
(C)
(D)
(E)
(F)
2).ReactionsPartB.Showthereagentsforthefollowingreactions.Chose5ofthe6,andmakesuretocirclethoseyouwantgraded.Ifyoudonotcircle,wewillgradethefirst5.(20points,4each)
OH
OH
O
O
O
Br
Br
Br
(A)
(B)
(C)
N3
3)ConceptQuestion.ThefollowingreactionsillustratetwodifferenteliminationproductsthatarisefromE2eliminationfromtwodifferentdiastereomers.Explainthisdifference,usingstructuresandmechanismstohelpsupportyouranswers(10points)
Br
Br NaNH2
NaNH2 major product
major product
4)Mechanisms.Showthemechanismof3ofthefollowing4reactions.Makesuretocirclethe3youwouldlikegraded.Otherwise,wewillgradethefirst3.(30points,10pointseach.
H2SO4
H2O
OH
(a)
4)Mechanisms(Continued)
MeH2SO4
H2O
Me OH
(b)
H2N NH(c)
Br2
heat
Br(d)
5)Synthesis.Proposeaseriesofreactionsthatwouldhelpcarryoutthefollowingsynthesis.(20points,10pointseach)(a)
CN
(b)